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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:19 UTC
HMDB IDHMDB0000947
Secondary Accession Numbers
  • HMDB00947
Metabolite Identification
Common NameUndecanoic acid
DescriptionUndecanoic acid, also known as N-undecylic acid or N-undecanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Undecanoic acid is a potentially toxic compound.
Structure
Data?1676999719
Synonyms
ValueSource
1-Decanecarboxylic acidChEBI
CH3-[CH2]9-COOHChEBI
Hendecanoic acidChEBI
N-Undecanoic acidChEBI
N-Undecoic acidChEBI
N-Undecylic acidChEBI
UDAChEBI
Undecoic acidChEBI
Undecylic acidChEBI
UndekansaeureChEBI
1-DecanecarboxylateGenerator
HendecanoateGenerator
N-UndecanoateGenerator
N-UndecoateGenerator
N-UndecylateGenerator
UndecoateGenerator
UndecylateGenerator
UndecanoateGenerator
1N-Undecoic acidHMDB
FA(11:0)HMDB
Undecanoic acidMeSH
Chemical FormulaC11H22O2
Average Molecular Weight186.2912
Monoisotopic Molecular Weight186.161979948
IUPAC Nameundecanoic acid
Traditional Nameundecanoic acid
CAS Registry Number112-37-8
SMILES
CCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
InChI KeyZDPHROOEEOARMN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point28.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 mg/mLNot Available
LogP4.42SANGSTER (1993)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg148.8730932474
[M-H]-Not Available148.87http://allccs.zhulab.cn/database/detail?ID=AllCCS00000230
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.49ALOGPS
logP4.03ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity54.08 m³·mol⁻¹ChemAxon
Polarizability23.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.14131661259
DarkChem[M-H]-144.81231661259
AllCCS[M+H]+148.18732859911
AllCCS[M-H]-149.56632859911
DeepCCS[M+H]+147.57630932474
DeepCCS[M-H]-143.9930932474
DeepCCS[M-2H]-180.99730932474
DeepCCS[M+Na]+156.38730932474
AllCCS[M+H]+148.232859911
AllCCS[M+H-H2O]+144.532859911
AllCCS[M+NH4]+151.732859911
AllCCS[M+Na]+152.732859911
AllCCS[M-H]-149.632859911
AllCCS[M+Na-2H]-151.032859911
AllCCS[M+HCOO]-152.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Undecanoic acidCCCCCCCCCCC(O)=O2350.0Standard polar33892256
Undecanoic acidCCCCCCCCCCC(O)=O1448.6Standard non polar33892256
Undecanoic acidCCCCCCCCCCC(O)=O1482.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Undecanoic acid,1TMS,isomer #1CCCCCCCCCCC(=O)O[Si](C)(C)C1552.6Semi standard non polar33892256
Undecanoic acid,1TBDMS,isomer #1CCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C1779.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Undecanoic acid GC-MS (1 TMS)splash10-0159-2910000000-722a87fa01fa27b58b072014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecanoic acid EI-B (Non-derivatized)splash10-0706-9000000000-d7f6a00a2bcfd58539f52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecanoic acid GC-MS (Non-derivatized)splash10-0159-2910000000-722a87fa01fa27b58b072017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r6-9400000000-c452aa611294afd4b2272016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9310000000-90668bb3fcf413ecc7672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecanoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-e152e90785434b58612c2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000i-0900000000-4e46062530f2b87127f22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-001i-2900000000-1bd11599567676fd18b82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0019-3900000000-3ed16e9aae084b8128f72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0706-9000000000-f0f2855ce0a7d3e0e44c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-000i-0900000000-70bc980554bccc2d565f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-0900000000-1923c2ee9004b1a4f2172012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-0900000000-818107787c04dbc613be2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-01t9-9000000000-da3c8186be5724d142622012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-052f-9000000000-4a1e2f342d24eb6ec79e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid ESI-TOF 10V, Negative-QTOFsplash10-03di-0090000000-2dadd8baad50427686a72017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid ESI-TOF 20V, Negative-QTOFsplash10-03di-0090000000-2dadd8baad50427686a72017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid ESI-TOF , Negative-QTOFsplash10-000i-0900000000-d09512035285f332d56c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid ESI-TOF 10V, Negative-QTOFsplash10-000i-0900000000-fca225c5971e85f0f1212017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid ESI-TOF 20V, Negative-QTOFsplash10-000i-0900000000-0fabd46bd1eaa73e5af02017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid ESI-TOF , Negative-QTOFsplash10-000i-0900000000-d09512035285f332d56c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-70bc980554bccc2d565f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-1923c2ee9004b1a4f2172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-f871962b32a5d16913f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecanoic acid LC-ESI-QQ , negative-QTOFsplash10-01t9-9000000000-f75b1abf45a6ce1d1e162017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanoic acid 10V, Positive-QTOFsplash10-00kr-0900000000-5e1b204d52a76537f6dd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanoic acid 20V, Positive-QTOFsplash10-000f-4900000000-4156178f661bac3b87852016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanoic acid 40V, Positive-QTOFsplash10-052f-9000000000-8f8e8441132607db272a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanoic acid 10V, Negative-QTOFsplash10-000i-0900000000-36794ad067903d2b66242016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanoic acid 20V, Negative-QTOFsplash10-000l-1900000000-157dc43c0ad4ff0f55092016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecanoic acid 40V, Negative-QTOFsplash10-0a4l-9300000000-95af6ebcd3a0e83715bd2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000700
KNApSAcK IDC00007421
Chemspider ID7888
KEGG Compound IDC17715
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUndecylic_acid
METLIN ID5894
PubChem Compound8180
PDB IDNot Available
ChEBI ID32368
Food Biomarker OntologyNot Available
VMH IDM03117
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSchreyer, Gerd; Schwarze, Werner; Weigert, Wolfgang. Carboxylic acids by oxidation of vicinal diols. Ger. Offen. (1972), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Avrahami D, Shai Y: Conjugation of a magainin analogue with lipophilic acids controls hydrophobicity, solution assembly, and cell selectivity. Biochemistry. 2002 Feb 19;41(7):2254-63. [PubMed:11841217 ]
  2. Avrahami D, Shai Y: Bestowing antifungal and antibacterial activities by lipophilic acid conjugation to D,L-amino acid-containing antimicrobial peptides: a plausible mode of action. Biochemistry. 2003 Dec 23;42(50):14946-56. [PubMed:14674771 ]
  3. Mingrone G, Greco AV, Capristo E, Benedetti G, Castagneto M, Gasbarrini G: An improved GLC method for a rapid, simultaneous analysis of both medium chain fatty acids and medium chain triglycerides in plasma. Clin Chim Acta. 1995 Sep 15;240(2):195-207. [PubMed:8548929 ]
  4. Kinkaid AR, Wilton DC: A continuous fluorescence displacement assay for phospholipase A2 using albumin and medium chain phospholipid substrates. Anal Biochem. 1993 Jul;212(1):65-70. [PubMed:8368517 ]
  5. Hamfler HW, Nissen HP, Heinze I, Kreysel HW, Schirren C: [Free fatty acid composition of human semen in different clinical diagnoses]. Andrologia. 1978 Nov-Dec;10(6):498-50. [PubMed:736283 ]
  6. Mosley EE, Wright AL, McGuire MK, McGuire MA: trans Fatty acids in milk produced by women in the United States. Am J Clin Nutr. 2005 Dec;82(6):1292-7. [PubMed:16332663 ]
  7. Hornung B, Amtmann E, Sauer G: Medium chain length fatty acids stimulate triacylglycerol synthesis in tissue culture cells. Biochem Pharmacol. 1992 Jan 22;43(2):175-81. [PubMed:1739406 ]
  8. Dutta-Roy AK, Demarco AC, Raha SK, Shay J, Garvey M, Horrobin DF: Effects of linoleic and gamma-linolenic acids (efamol evening primrose oil) on fatty acid-binding proteins of rat liver. Mol Cell Biochem. 1990 Oct 15-Nov 8;98(1-2):177-82. [PubMed:2176271 ]
  9. (). Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990. .

Enzymes

General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ACSM6
Uniprot ID:
Q6P461
Molecular weight:
53584.545
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM2A
Uniprot ID:
Q08AH3
Molecular weight:
64223.7
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:
ACSM2B
Uniprot ID:
Q68CK6
Molecular weight:
64270.78
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM3
Uniprot ID:
Q53FZ2
Molecular weight:
66152.235
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM5
Uniprot ID:
Q6NUN0
Molecular weight:
64759.55
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM4
Uniprot ID:
P0C7M7
Molecular weight:
65702.225